Cheapest return flights from Chicago to San Juan in December from 349€

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in December 2025 (see full year).

Return flights

06 Dec - 11 Dec Southwest Airlines
05 Dec - 11 Dec Southwest Airlines
14 Dec - 18 Dec Southwest Airlines
28 Dec - 03 Jan Southwest Airlines
26 Dec - 02 Jan Southwest Airlines

Also check the deals for one-way flights from Chicago to San Juan in December.

Skyscanner

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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